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North of Roosevelt Road and east of the Chicago River's South Branch, an enourmous crane marks the future site of another South Loop residential development.

The historical irony here is that the neighborhood known today as the South Loop originally had a resi-dential flavor, beginning in 1836—one year before Chicago incorporated as a city—when Henry Clarke built a house near what is now 16th and Michigan (the house, Chicago’s second oldest, has been moved to 1855 South Indiana Avenue). In the 1880s, several of Chicago’s Gilded Age titans—among them, the piano maker William Kimball, the merchant Marshall Field, and the railcar builder George Pullman—built baronial homes along Prairie Avenue near 18th Street, making it the city’s most stylish neighborhood for a decade or so.
Meanwhile, just four blocks west, the Levee—the city’s most infamous vice district—was thriving. The 1894 book If Christ Came to Chicago, which portrayed the sin and depravity of urban life, focused much of its attention on the district’s brothels and gambling parlors, which proved more enduring than the stone palaces of Prairie Avenue.

At the beginning of the 20th century, as wealthy Chicagoans began heading north to the present-day Gold Coast, industries supplanted homeowners as the primary residents of the South Loop. Some of the city’s—indeed, the country’s—biggest companies were represented there, including International Harvester, Crane Plumbing, R. R. Donnelley publishing, and Studebaker automobiles. But there were also other, lesser-known enterprises operating on a big scale, producing such essential modern contrivances as hairpins. The area was also a major rail center, home to four of Chicago’s six big train depots.

A new era began in the decades following World War II as rail travel declined and industry drifted away to newer locations, leaving behind many gorgeous but vacant buildings and miles of railroad tracks. By 1954, the neighborhood had faded so much that the Chicago Tribune referred to it as a “tattered doll in sequins.”

Saddled with this moniker, the South Loop spent years as a palimpsest upon which urban dreamers could project their wildest schemes. In 1968, a team of developers whipped up plans for Chicago’s Garden-in-the-Sky, a dense pack of 13 towers—50 to 73 stories high, home to offices, apartments, and a hotel—a mammoth multisport stadium, and two huge shopping malls, all crammed onto about 12 square blocks around Congress Parkway and State Street. The project never materialized—which didn’t deter another development team from proposing in 1974 a futuristic South Loop New Town, with glass-tube walkways five flights above the street and monorail trains running beneath cantilevered residential terraces. That plan didn’t fly either.

In 1977, yet another team trotted out River City, which would have put six interconnected 72-story towers—with apartments for about 45,000 people—on the east bank of the river’s South Branch. All that came of it was a single 17-story structure completed in 1986, Bertrand Goldberg’s curvaceous building, called River City, which still stands on the river at 800 South Wells Street. Then there was the futile attempt to organize a 1992 world’s fair on the south lakefront, and, in 1986, a short-lived plan, floated by Harold Washington’s administration, to build a stadium complex in the neighborhood.

Each one of those plans has trumpeted the South Loop’s many virtues, and in retrospect, it’s a little surprising the area’s development wasn’t more of a slam dunk. It lies adjacent to the Loop, with its jobs and cultural activities, and to the gorgeous but underused south lakefront. Expressways and public transportation are right at its doorstep, and development would not entail pushing out an existing population. Despite these obvious advantages, the area’s modernization was slow, as, one by one, pieces fell into place, building momentum for the big boom of the past decade.

The first piece of the puzzle was Dearborn Park I, eight square blocks of townhouses, mid-rises, and parks finished in the mid-1980s between the rehabbed Dearborn Station and Roosevelt Road. (The development of Dearborn Park and the reinvigoration of Chicago’s downtown were the subjects of Lois Wille’s 1997 book, At Home in the Loop.) Completed in the mid-1980s, the buildings were nice but inward looking, as befitted a pioneering attempt to bring residential life into a shabby area.

Meanwhile, in an area extending north from Dearborn Station to Congress Parkway, urban pioneers were reinventing the beautiful buildings from Chicago’s early-1900s heyday as the nation’s printer, in the process creating the city’s first residential loft neighborhood. Together, these two pieces created a beachhead of South Loop life, and also set the tone for the neighborhood’s appealing mix of old and new architecture. In the late 1980s, Dearborn Park II appeared, extending from Roosevelt Road to 15th Street. Confidence in the neighborhood was clearly rising; here, the houses were bigger, the streets more open to public use.

Other small developments—a loft conversion here, a string of townhouses there—tried hard to pull attention south of Congress, but none had enough heft. Then came the 1990s and a confluence of low interest rates (fueling home construction), a reconfigured Lake Shore Drive and Roosevelt Road, and a newly rediscovered love of city life. The floodgates opened, and developers poured into the South Loop, with eager homebuyers hot on their heels.


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